Next Article in Journal
Preparation of Poly-1-butene Nanofiber Mat and Its Application as Shutdown Layer of Next Generation Lithium Ion Battery
Next Article in Special Issue
Thermoresponsive Polymers of Poly(2-(N-alkylacrylamide)ethyl acetate)s
Previous Article in Journal
Basic Research for Additive Manufacturing of Rubber
Previous Article in Special Issue
Microfluidic Fabrication of Monodisperse Microcapsules for Thermo-Triggered Release of Liposoluble Drugs
Article

Micellar Organocatalysis Using Smart Polymer Supports: Influence of Thermoresponsive Self-Assembly on Catalytic Activity

Department of Chemistry, Paderborn University, Warburger Str. 100, D-33098 Paderborn, Germany
*
Author to whom correspondence should be addressed.
Polymers 2020, 12(10), 2265; https://doi.org/10.3390/polym12102265
Received: 4 September 2020 / Revised: 23 September 2020 / Accepted: 29 September 2020 / Published: 1 October 2020
(This article belongs to the Special Issue Thermoresponsive Polymers)
Micellar catalysts with a switchable core are attractive materials in organic synthesis. However, little is known about the role of the shell forming block on the performance of the catalyst. Thermoresponsive block copolymers based on poly(N-isopropylacrylamide-co-vinyl-4,4-dimethylazlactone) attached to different permanently hydrophilic blocks, namely poly(ethylene glycol), poly(N,N-dimethylacrylamide), and poly(2,3-dihydroxypropyl acrylate), were successfully synthesized via reversible addition/fragmentation chain transfer radical polymerization (RAFT). Post-polymerization attachment of an amino-functionalized L-prolineamide using the azlactone ring-opening reaction afforded functionalized thermoresponsive block copolymers. Temperature-induced aggregation of the functionalized block copolymers was studied using dynamic light scattering. It was shown that the chemical structure of the permanently hydrophilic block significantly affected the size of the polymer self-assemblies. The functionalized block copolymers were subjected to an aldol reaction between p-nitrobenzaldehyde and cyclohexanone in water. Upon temperature-induced aggregation, an increase in conversion was observed. The enantioselectivity of the polymer-bound organocatalyst improved with an increasing hydrophilic/hydrophobic interface as a result of the different stability of the polymer aggregates. View Full-Text
Keywords: thermoresponsive block copolymers; azlactone ring-opening; immobilized L-prolineamide; RAFT polymerization; temperature-induced self-assembly; micellar organocatalysis thermoresponsive block copolymers; azlactone ring-opening; immobilized L-prolineamide; RAFT polymerization; temperature-induced self-assembly; micellar organocatalysis
Show Figures

Graphical abstract

MDPI and ACS Style

Yu, X.; Herberg, A.; Kuckling, D. Micellar Organocatalysis Using Smart Polymer Supports: Influence of Thermoresponsive Self-Assembly on Catalytic Activity. Polymers 2020, 12, 2265. https://doi.org/10.3390/polym12102265

AMA Style

Yu X, Herberg A, Kuckling D. Micellar Organocatalysis Using Smart Polymer Supports: Influence of Thermoresponsive Self-Assembly on Catalytic Activity. Polymers. 2020; 12(10):2265. https://doi.org/10.3390/polym12102265

Chicago/Turabian Style

Yu, Xiaoqian, Artjom Herberg, and Dirk Kuckling. 2020. "Micellar Organocatalysis Using Smart Polymer Supports: Influence of Thermoresponsive Self-Assembly on Catalytic Activity" Polymers 12, no. 10: 2265. https://doi.org/10.3390/polym12102265

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop